The cost of Quicken was never my problem. It was the forced upgrades that bothered me. I always encountered some type of issue after upgrading and having to pay for that luxury wasn't worth it. Plus, I moved over to a Mac, where Quicken support is lacking.

I changed over to Moneydance, which works well and is truly cross platform with no forced upgrades. It might not have all the bells and whistles of Quicken, but once you learn it's quirks - and all of these programs have their own set of quirks - it works well for what I need. I even paid for an upgrade after a couple of years, which went smoothly. Except for one issue, which when I e-mailed them about was answered quickly. I doubt I'd get the same level of customer service from Intuit.

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I don't see spending $70 or so every three years for an upgrade as a burden given the functionality I get from Quicken.

For me, maintenance is a breeze. Virtually every account I have is defined to Quicken so I kick-off One Step Update and then review/accept transactions. Usually 5 minutes or so two-three times a week to have up to date data.

The other nice thing about having everything in Quicken is I can easily monitor our long-term forecast through Lifetime Planner.

Cash is split between a cash management account at Fidelity, which we use like a bank, and Ally, where we earn 0.9% on money we won't need for a year or more.

The cost of Quicken was never the issue. It was the disabling of online capabilities. It they want to stop supporting, that's fine. But to render the software useless is unacceptable. Plus, the free online tools do everything I need and are easier to use.

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